Diethyl Ether → [2-(Benzyloxy)-5-formylphenyl]methyl methanesulfonate

HRID 2213573Notes

Reaction equation

HRID 2213573 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[OH:6][CH2:7][C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][C:15]=1[O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH:11]=[O:12].C(N(C(C)C)CC)(C)C.C(OCC)C>ClCCl>[CH3:1][S:2]([O:6][CH2:7][C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][C:15]=1[O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH:11]=[O:12])(=[O:4])=[O:3]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 21957471HCID 21957471, compound

Product 1

HCID 21957468[2-(Benzyloxy)-5-formylphenyl]methyl methanesulfonateYield 85.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulfonyl chloride (2.50 g) was added to a stirred solution of 3-(hydroxymethyl)-4-phenylmethoxybenzaldehyde (4.00 g) in dichloromethane (50 ml) at 0° C. To this solution was then added diisopropylethylamine (8.1 ml) over approx. 2 minutes. After stirring for a further 5 minutes the reaction mixture was partitioned between dichloromethane and water. The organic layer was washed with dilute hydrochloric acid, dried over sodium sulfate, filtered and concentrated under reduced pressure to give pale straw coloured oil. Addition of diethyl ether caused the product to crystallize. This material was collected and washed with more diethyl ether to give 3-[[(methylsulfonyl)oxy]methyl]-4-phenylmethoxybenzaldehyde (4.51 g) as off-white crystals. 1H NMR (CDCl3) δ 9.78 (s, 1H, CHO); 5.22 (s, 2H); 5.10 (s, 2H); 2.83 (s, 3H). TLC (silica gel): Rf=0.4 (dichloromethane:diethyl ether, 24:1).

Workup

  1. customwas partitioned between dichloromethane and water
  2. washThe organic layer was washed with dilute hydrochloric acid
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto give pale straw coloured oil
  7. customto crystallize
  8. customThis material was collected
  9. washwashed with more diethyl ether

Sources & evidence

ORD record
ord-233c629fb6cd43e385578283c331f174
Source dataset
uspto-grants-2006_09
Patent number
US07105554B2

Reaction notes

Loading…